CN107522704A - Compounds, the photosensitive resin composition and colored filter for including it - Google Patents

Compounds, the photosensitive resin composition and colored filter for including it Download PDF

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Publication number
CN107522704A
CN107522704A CN201710177372.5A CN201710177372A CN107522704A CN 107522704 A CN107522704 A CN 107522704A CN 201710177372 A CN201710177372 A CN 201710177372A CN 107522704 A CN107522704 A CN 107522704A
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Prior art keywords
chemical formula
represented
compound
resin composition
photosensitive resin
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CN201710177372.5A
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CN107522704B (en
Inventor
郑义树
徐惠瑗
辛明晔
申先雄
郑周昊
韩圭奭
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Samsung SDI Co Ltd
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Samsung SDI Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/085—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex substituting the central metal atom
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)

Abstract

The present invention provides a kind of compound represented by chemical formula 1, the photosensitive resin composition comprising it and the colored filter manufactured using the photosensitive resin composition.In chemical formula 1, each substituent is identical with defined in specification.The compound represented by chemical formula 1 has the splendid solubility in splendid green spectral characteristic, higher molar extinction coefficient and organic solvent, and it therefore can be used as the dyestuff of the green photonasty resin combination for colored filter, and therefore, the colored filter comprising dyestuff can have splendid color intensity, transmissivity, brightness and contrast ratio.[chemical formula 1]

Description

Compounds, the photosensitive resin composition and colored filter for including it
The cross reference of related application
The korean patent application 10-2016- submitted this application claims on June 16th, 2016 in Korean Intellectual Property Office The korean patent application that the priority and rights and interests of No. 0075318 and on January 9th, 2017 submit in Korean Intellectual Property Office The rights and interests of No. 10-2017-0003109, its whole includes to be incorporated herein in a manner of introducing.
Technical field
The present invention relates to compounds including its photosensitive resin composition and colored filter.
Background technology
In the display of many types, the advantage of liquid crystal display device is brightness, thinness, low cost, low operating work Consumption and the adhesiveness improvement to integrated circuit, and it has been more broadly used for notebook computer, monitor and TV screens.Liquid Crystal device includes lower substrate, has been formed thereon black matix, colored filter and ITO pixel electrodes；With it is upper Portion's substrate, has been formed thereon active circuitry region and ITO pixel electrodes, and the active circuitry region includes liquid crystal layer, thin Film transistor and capacitor layer.
By sequentially stacking multiple colored filters with predesigned order (in general, by three kinds of primary colors in pixel region Formed, such as red (R), green (G) and blue (B)) to form each pixel to form colored filter, and in transparent substrates On dispose black matrix layer in a predetermined pattern to form the border between pixel.(it is colored filter shape to pigment dispersion method Into one of method) it is to provide colorful film by repeating series of process, such as applied on the transparency carrier comprising black matix Photopolymerizable constituent of the cloth comprising colouring agent, make formed pattern exposure, unexposed portion is removed with solvent and makes it Heat cure.Colored photosensitive polymer combination for manufacturing colored filter according to pigment dispersion method generally comprises alkali solubility Resin, photo polymerization monomer, photopolymerization initiator, epoxy resin, solvent, other additives etc..Pigment dispersion method is by energetically For manufacturing LCD, such as mobile phone, notebook computer, monitor and TV.However, for pigment dispersion method, for colour The photosensitive resin composition of optical filter needs to have improved properties recently and splendid pattern contour.Exactly, urgently Need higher colorrendering quality and higher brightness and high contrast ratio feature.
In addition, the colored filter manufactured using color type photosensitive resin composition is because of pigment particle size and in brightness and right Limitation in terms of ratio be present.In addition, the color image sensor device for imaging sensor needs smaller dispersed particle diameter To form fine pattern.In order to meet the requirements, do not form the dyes instead of pigments of particle by introducing, be applied to so as to prepare The photosensitive resin composition of dyestuff has the colored filter of improved brightness and contrast ratio to attempt acquisition.Therefore, it is necessary to It is suitable for preparing the compound of the dyestuff of photosensitive resin composition and includes its photosensitive resin composition.
The content of the invention
One embodiment provides a kind of compounds.
Another embodiment provides a kind of photosensitive resin composition for including the compound.
Another embodiment provides a kind of colored filter manufactured using the photosensitive resin composition.
One embodiment provides a kind of compound represented by chemical formula 1.
[chemical formula 1]
In chemical formula 1,
R1To R16Be independently hydrogen atom, halogen atom, C1 to the C20 alkyl for being substituted or being unsubstituted, be substituted or C3 to the C20 alkoxies being unsubstituted, C6 to the C20 aryl for being substituted or being unsubstituted or the C6 that is substituted or is unsubstituted are arrived C20 aryloxy group,
Restrictive condition is R1To R16In it is at least one represented by chemical formula 2,
[chemical formula 2]
Wherein in chemical formula 2,
R17And R18It is independently halogen atom,
N1 and n2 is independently the integer in the range of 0 to 5, and 1≤n1+n2≤5.
Chemical formula 2 can be represented by one selected in chemical formula 3-1 to chemical formula 3-4.
[chemical formula 3-1]
[chemical formula 3-2]
[chemical formula 3-3]
[chemical formula 3-4]
Wherein, in chemical formula 3-1 to chemical formula 3-4,
R17And R18It is independently halogen atom.
R1To R16In it is at least one can be represented by chemical formula 2, and R1To R16In it is at least one can be by chemical formula 4 Represent.
[chemical formula 4]
R1To R16In it is at least one can be represented by chemical formula 2, R5To R8In it is at least one can be by the table of chemical formula 4 Show, R9To R12In it is at least one can be represented by chemical formula 4, and R13To R16In it is at least one can be by the table of chemical formula 4 Show.
R1To R4In it is at least one can be represented by chemical formula 2, R5To R8In it is at least one can be by the table of chemical formula 2 Show, R9To R12In it is at least one can be represented by chemical formula 4, and R13To R16In it is at least one can be by the table of chemical formula 4 Show.
R1To R4In it is at least one can be represented by chemical formula 2, R5To R8In it is at least one can be by the table of chemical formula 4 Show, R9To R12In it is at least one can be represented by chemical formula 2, and R13To R16In it is at least one can be by the table of chemical formula 4 Show.
R1To R4In it is at least one can be represented by chemical formula 2, R5To R8In it is at least one can be by the table of chemical formula 2 Show, R9To R12In it is at least one can be represented by chemical formula 2, and R13To R16In it is at least one can be by the table of chemical formula 4 Show.
R1To R4In it is at least one can be represented by chemical formula 2, R5To R8In it is at least one can be by the table of chemical formula 2 Show, R9To R12In it is at least one can be represented by chemical formula 2, and R13To R16In it is at least one can be by the table of chemical formula 2 Show.
The compound represented by chemical formula 1 can be by chemical formula 5 a to expression in chemical formula 14.
[chemical formula 5]
[chemical formula 6]
[chemical formula 7]
[chemical formula 8]
[chemical formula 9]
[chemical formula 10]
[chemical formula 11]
[chemical formula 12]
[chemical formula 13]
[chemical formula 14]
The compound can be green colouring material.
Green colouring material can have maximum transmission rate into 560 nanometer wavelength ranges at 445 nanometers.
Another embodiment provides the photosensitive resin composition for including the compound represented by chemical formula 1.
Photosensitive resin composition can include based on the total amount of photosensitive resin composition 1 weight % to 10 weight % amount The compound represented by chemical formula 1.
Photosensitive resin composition can further include adhesive resin, colouring agent, photopolymerizable compound, photopolymerization initiator And solvent.
Photosensitive resin composition can further include pigment.
Pigment can include yellow uitramarine, viridine green or its combination.
Another embodiment provides and uses colored filter made of photosensitive resin composition.
Other embodiments of the invention include in the following specific embodiments.
Splendid green spectral characteristic, higher molar extinction coefficient and organic molten are had according to the compound of one embodiment Splendid solubility in agent, and therefore can be used as the dyestuff of the green photonasty resin combination for colored filter, and because This, the colored filter comprising dyestuff can have splendid color intensity, transmissivity, brightness and contrast ratio.
Embodiment
Hereinafter, embodiments of the invention are described in detail.However, these embodiments are exemplary, the invention is not restricted to This and the present invention is defined by the category of claim.
As used herein, when offer is not specifically defined in addition, term " substitution " refers to by by the following substitution selected Base substitutes：Halogen (F, Br, Cl or I), hydroxyl, nitro, cyano group, amino (NH2、NH(R200) or N (R201)(R202), wherein R200、 R201And R202It is identical or different, and be independently C1 to C10 alkyl), carbonamidine base, diazanyl, hydrazone group, carboxyl, be substituted or not The alkyl that is substituted, the alkenyl for being substituted or being unsubstituted, the alkynyl that is substituted or is unsubstituted, it is substituted or is unsubstituted Alicyclic organic group, the aryl for being substituted or being unsubstituted and the heterocyclic radical for being substituted or being unsubstituted.
As used herein, when offer is not specifically defined in addition, term " alkyl " refers to C1 to C20 alkyl and especially C1 To C15 alkyl, term " cycloalkyl " refers to C3 to C20 cycloalkyl and especially C3 to C18 cycloalkyl, and term " alkoxy " refers to C1 To C20 alkoxies and especially C1 to C18 alkoxies, term " aryl " refer to C6 to C20 aryl and especially C6 to C18 aryl, art Language " alkenyl " refers to C2 to C20 alkenyls and especially C2 to C18 alkenyls, and term " alkylidene " refers to C1 to C20 alkylidenes and especially C1 to C18 alkylidenes, and term " arlydene " refers to C6 to C20 arlydene and especially C6 to C16 arlydene.
As used herein, when in addition provide be specifically defined when, " (methyl) acrylate " refer to " acrylate " and " methacrylate ", and " (methyl) acrylic acid " refers to " acrylic acid " and " methacrylic acid ".
As used herein, when not otherwise provided definitions, term " combination " refers to mixing or combined polymerization.In addition, " copolymerization Close " refer to block copolymerization to random copolymerization, and " copolymer " refers to block copolymer to random copolymer.
In the chemical formula of this specification, it is specifically defined unless otherwise provided, otherwise when chemical bond is in the position that should be provided When place is not drawn, hydrogen bond knot is in the opening position.
As used herein, when in addition provide be specifically defined when, " * " instruction be wherein connected with identical or different atom or The point of chemical formula.
One embodiment provides a kind of compound represented by chemical formula 1.
[chemical formula 1]
In chemical formula 1,
R1To R16Be independently hydrogen atom, halogen atom, C1 to the C20 alkyl for being substituted or being unsubstituted, be substituted or C3 to the C20 alkoxies being unsubstituted, C6 to the C20 aryl for being substituted or being unsubstituted or the C6 that is substituted or is unsubstituted are arrived C20 aryloxy group,
Restrictive condition is R1To R16In it is at least one represented by chemical formula 2,
[chemical formula 2]
In chemical formula 2,
R17And R18It is independently halogen atom,
N1 and n2 is independently the integer in the range of 0 to 5, and 1≤n1+n2≤5.
The compound represented by chemical formula 1 has splendid green spectral characteristic and higher molar extinction coefficient.In addition, applying During being added to colored filter, by necessarily including the substituent represented by chemical formula 2, the compound represented by chemical formula 1 There is splendid solubility and premium brightness and contrast ratio in organic solvent.
Chemical formula 2 can be represented by one selected in chemical formula 3-1 to chemical formula 3-4.
[chemical formula 3-1]
[chemical formula 3-2]
[chemical formula 3-3]
[chemical formula 3-4]
Wherein, in chemical formula 3-1 to chemical formula 3-4,
R17And R18It is independently halogen atom.
The substituent represented by chemical formula 3-1 to 3-4 is the aryloxy group substituted through at least one halogen atom, and herein In when at least one halogen atom especially ortho position and/or contraposition substituted when, brightness and contrast ratio can be improved further. In addition, when halogen atom is all substituted at ortho position and contraposition (two halogen atoms are substituted), brightness and contrast ratio can With with halogen atom only ortho position or contraposition (halogen atom is substituted) substituted when compared be greatly improved.So And when halogen atom is substituted in meta (also being substituted at ortho position and/or contraposition even if another halogen atom), brightness Being improved with contrast ratio may unobvious.
In other words, in the substituent represented by chemical formula 2, such as in the substituent represented by chemical formula 3-1 to 3-4 In, brightness and contrast ratio can be improved with following order (i → ii → iii)；I) at least one halogen atom is carried out in meta Substitution, ii) halogen atom ortho position or contraposition substituted, and iii) halogen ortho position and contraposition all substituted.
R1To R16In it is at least one can be represented by chemical formula 2, and R1To R16In it is at least one can be by chemical formula 4 Represent.
[chemical formula 4]
For example, the substituent represented by chemical formula 4 can be represented by chemical formula 4-1.
[chemical formula 4-1]
R1To R4In it is at least one can be represented by chemical formula 2, R5To R8In it is at least one can be by the table of chemical formula 4 Show, R9To R12In it is at least one can be represented by chemical formula 4, and R13To R16In it is at least one can be by the table of chemical formula 4 Show.
For example, R2Or R3It can be represented by chemical formula 2, R6Or R7It can be represented by chemical formula 4, R10Or R11Can be by Chemical formula 4 represents, and R14Or R15It can be represented by chemical formula 4.
For example, R2Or R3It can be represented by chemical formula 2, R6Or R7It can be represented by chemical formula 4, R10Or R11Can be by Chemical formula 4 represents, R14Or R15It can be represented by chemical formula 4, and the residue not represented by chemical formula 2 and chemical formula 4 can be all It is halogen atom.
R1To R4In it is at least one can be represented by chemical formula 2, R5To R8In it is at least one can be by the table of chemical formula 2 Show, R9To R12In it is at least one can be represented by chemical formula 4, and R13To R16In it is at least one can be by the table of chemical formula 4 Show.
For example, R2Or R3It can be represented by chemical formula 2, R6Or R7It can be represented by chemical formula 2, R10Or R11Can be by Chemical formula 4 represents, and R14Or R15It can be represented by chemical formula 4.
For example, R2Or R3It can be represented by chemical formula 2, R6Or R7It can be represented by chemical formula 2, R10Or R11Can be by Chemical formula 4 represents, R14Or R15It can be represented by chemical formula 4, and the residue not represented by chemical formula 2 and chemical formula 4 can be all It is halogen atom.
R1To R4In it is at least one can be represented by chemical formula 2, R5To R8In it is at least one can be by the table of chemical formula 4 Show, R9To R12In it is at least one can be represented by chemical formula 2, and R13To R16In it is at least one can be by the table of chemical formula 4 Show.
For example, R2Or R3It can be represented by chemical formula 2, R6Or R7It can be represented by chemical formula 4, R10Or R11Can be by Chemical formula 2 represents, and R14Or R15It can be represented by chemical formula 4.
For example, R2Or R3It can be represented by chemical formula 2, R6Or R7It can be represented by chemical formula 4, R10Or R11Can be by Chemical formula 2 represents, R14Or R15It can be represented by chemical formula 4, and the residue not represented by chemical formula 2 and chemical formula 4 can be all It is halogen atom.
R1To R4In it is at least one can be represented by chemical formula 2, R5To R8In it is at least one can be by the table of chemical formula 2 Show, R9To R12In it is at least one can be represented by chemical formula 2, and R13To R16In it is at least one can be by the table of chemical formula 4 Show.
For example, R2Or R3It can be represented by chemical formula 2, R6Or R7It can be represented by chemical formula 2, R10Or R11Can be by Chemical formula 2 represents, and R14Or R15It can be represented by chemical formula 4.
For example, R2Or R3It can be represented by chemical formula 2, R6Or R7It can be represented by chemical formula 2, R10Or R11Can be by Chemical formula 2 represents, R14Or R15It can be represented by chemical formula 4, and the residue not represented by chemical formula 2 and chemical formula 4 can be all It is halogen atom.
R1To R4In it is at least one can be represented by chemical formula 2, R5To R8In it is at least one can be by the table of chemical formula 2 Show, R9To R12In it is at least one can be represented by chemical formula 2, and R13To R16In it is at least one can be by the table of chemical formula 2 Show.
For example, R2Or R3It can be represented by chemical formula 2, R6Or R7It can be represented by chemical formula 2, R10Or R11Can be by Chemical formula 2 represents, and R14Or R15It can be represented by chemical formula 2.
For example, R2Or R3It can be represented by chemical formula 2, R6Or R7It can be represented by chemical formula 2, R10Or R11Can be by Chemical formula 2 represents, R14Or R15It can be represented by chemical formula 2, and the residue not represented by chemical formula 2 can all be halogen original Son.
For example, the compound represented by chemical formula 1 can by chemical formula 5 to one in chemical formula 14 expression, but Not limited to this.
[chemical formula 5]
[chemical formula 6]
[chemical formula 7]
[chemical formula 8]
[chemical formula 9]
[chemical formula 10]
[chemical formula 11]
[chemical formula 12]
[chemical formula 13]
[chemical formula 14]
Even if according to the compound of one embodiment can still show apparent color on a small quantity, and when as colouring agent, Can be by having comprising one in the substituent represented by chemical formula 2, such as chemical formula 3-1 to chemical formula 3-4 to manufacture Such as display device of the splendid color characteristic of brightness, contrast ratio.For example, compound can be colouring agent, such as dyestuff, example Such as green colouring material, such as there are at 445 nanometers the dyestuffs of maximum transmission rate into 560 nanometer wavelength ranges.In addition, green colouring material It can be the dyestuff into 730 nanometer wavelength ranges at 600 nanometers with maximum absorbance.
In general, dyestuff is for most expensive in the component in colored filter.Therefore, the expensive dyestuff may Need more realizing required effect, such as high brightness, high-contrast etc. and the unit cost for therefore increasing production.However, When the dyestuff being used as according to the compound of one embodiment in colouring agent, such as colored filter, the compound and/or poly- Even if compound can still realize improved color character (such as high brightness or high contrast ratio) and reduction production of units with a small amount of use Cost.
According to another embodiment, photosensitive resin composition includes the compound according to one embodiment.
For example, photosensitive resin composition includes：Include the colouring agent of the compound according to embodiment；Adhesive tree Fat；Photopolymerizable compound；Photopolymerization initiator；And solvent.
Hereinafter specifically describe every kind of component.
Colouring agent
Colouring agent can include the compound according to embodiment.
Colouring agent can further include viridine green and/or yellow uitramarine.
For example, colouring agent can include compound, viridine green dispersion liquid and the yellow uitramarine represented by chemical formula 1 Dispersion liquid, and the compound represented by chemical formula 1 can be necessarily comprising the substituent represented by chemical formula 2.
Because green colouring material has maximum transmission rate into 560 nanometer wavelength ranges at 445 nanometers, and is arrived at 600 nanometers There is maximum absorbance, when green colouring material and viridine green dispersion liquid and Yellow Pigment Dispersion one in 730 nanometer wavelength ranges Rise when being used as colouring agent, realize higher color coordinate, and coloring properties, brightness and contrast ratio can be improved.
Colouring agent can include compound, viridine green dispersion liquid and the Yellow Pigment Dispersion represented by chemical formula 1, its Amount is respectively the weight % of total amount meter 1 to 10 weight % (such as 3 weight % to 7 weight %), the 60 weight % to 70 according to toner Weight % and 20 weight % to 30 weight %.When in colouring agent include the amount in the range of the change represented by chemical formula 1 When compound, viridine green dispersion liquid and Yellow Pigment Dispersion, it is possible to achieve there is the colouring agent of improved coloring properties, and The colored filter with improved brightness and contrast ratio can also be realized.
For example, the viridine green in viridine green dispersion liquid can be C.I. naphthol greens 58 in color index, C.I. naphthol green 59 etc., it can be used alone or the form of mixtures with two kinds or more than two kinds uses.In addition, yellow uitramarine point Yellow uitramarine in dispersion liquid can be C.I. pigment yellow 13s 9, C.I. pigment yellow 13s 8, C.I. pigment yellows 150 in color index Deng it can be used alone or form of mixtures with two kinds or more than two kinds uses.
Baseline is lower in above-mentioned wave-length coverage, and higher transmissivity (brightness) is obtained in higher color region.For The absorption peak occurred between 600 nanometers to 730 nanometers, more peak value indicate higher color intensity, and herein, the present invention Dyestuff show about 1.5 times of high peaks and therefore have color higher compared with C.I. naphthol greens 58 and C.I. naphthol greens 59 strong Degree.In other words, when dyestuff and C.I. naphthol greens 58, C.I. naphthol greens 59, C.I. pigment yellow 13s 8 of the present invention etc. are used together When, it is possible to achieve higher color coloured silk coordinate.
In general, dyestuff is most expensive in the component for colored filter.Therefore, in order to realize required effect Fruit, such as high brightness, high contrast ratio etc., more using expensive dyestuff and it therefore should may increase unit manufacturing cost.However, work as When the compound of one embodiment is used as dyestuff in colored filter, even if the dyestuff can still realize splendid face on a small quantity with it Color characteristic, such as high brightness, high contrast ratio etc. and therefore reduce unit manufacturing cost.
Viridine green and/or yellow uitramarine can be used together with dispersant to disperse pigment.Exactly, can be in table With dispersant preconditioned pigment or addition pigment to prepare constituent on face.
Dispersant can be non-ionic dispersing agent, anionic dispersing agents, cation dispersing agent etc..The particular instance of dispersant Can be polyolefin diols and its ester, polyoxyalkylene, polyol ester oxirane additive product, alcohol oxirane additive product, sulfonic acid Ester, sulfonate, carboxylate, carboxylate, alkylamide oxirane additive product, alkylamine etc., and can be used alone or with two kinds Or the form of mixtures more than two kinds uses.
The commercial examples of dispersant can include the Di Sibike manufactured by Societe BIC S.A. (BYK Co., Ltd.s) (DISPERBYK) -101, Di Sibike -130, Di Sibike -140, Di Sibike -160, Di Sibike -161, Di Sibike - 162nd, Di Sibike -163, Di Sibike -164, Di Sibike -165, Di Sibike -166, Di Sibike -170, Di Sibi Grams -171, Di Sibike -182, Di Sibike -2000, Di Sibike -2001 etc.；By EFKA chemical company (EFKA Chemicals Co.) manufacture EFKA (EFKA) -47, EFKA -47EA, EFKA -48, EFKA -49, EFKA - 100th, EFKA -400, EFKA -450 etc.；The Suo Si Persian (Solsperse) manufactured by Ze Neika companies (ZenekaCo.) 5000th, Suo Si Persian 12000, Suo Si Persian 13240, Suo Si Persian 13940, Suo Si Persian 17000, Suo Si Persian 20000, rope This Persian 24000GR, Suo Si Persian 27000, Suo Si Persian 28000 etc.；Or by Ajincomoto Co., Inc (Ajinomoto Inc) PB711, PB821 of manufacture.
Based on the total amount of photosensitive resin composition, dispersant can be included with 0.1 weight % to 15 weight % amount. During dispersant in comprising the scope, during black column spacer is manufactured, improved dispersing characteristic is attributed to, is formed Thing has excellent stability, developability and pattern Forming ability.
Water-soluble inorganic salt and wetting agent pretreatment can be used in pigment.When preconditioned pigment, the averaged particles of pigment are straight Footpath can become thinner.
It can be entered by mediating pigment and water-soluble inorganic salt and wetting agent, and then filtering and wash the pigment mediated Row pretreatment.
It can be mediated at a temperature of 40 DEG C to 100 DEG C, and can be by after inorganic salts are washed away with water etc. Pigment is filtered to be filtered and be washed.
The example of water-soluble inorganic salt can be sodium chloride, potassium chloride etc., but not limited to this.Wetting agent can make pigment with it is water-soluble Property inorganic salts uniformly mixing and crush.The example of wetting agent includes alkane glycol monoalkyl ether, such as ethylene glycol monoethyl ether, propane diols Monomethyl ether, diethylene glycol monomethyl ether etc.；And alcohol, as ethanol, isopropanol, butanol, hexanol, cyclohexanol, ethylene glycol, diethylene glycol, Polyethylene glycol, glycerine polyethylene glycol etc..These can be used alone or the form of mixtures with two kinds or more than two kinds uses.
Pigment can have in about 5 nanometers to about 200 nanometers, e.g., from about 5 nanometers to about 150 nanometer ranges after kneading Mean particle diameter.When pigment has the mean particle diameter in the scope, the stability of dispersible pigment dispersion can be improved And pixel resolution may not deteriorate.
Solvent for forming dispersible pigment dispersion can be Ethylene glycol acetate, ethyl cellosolve, propylene glycol monomethyl ether acetic acid Ester, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol monomethyl ether etc..
Exactly, pigment can include and then use the dispersible pigment dispersion form of the dispersant of description and solvent, and The dispersible pigment dispersion can include solid pigment, dispersant and solvent.Based on the total amount of dispersible pigment dispersion, solid pigment can be with 5 weight % to 20 weight %, such as 8 weight % to 15 weight % amount are included.
Based on the total amount of photosensitive resin composition, dispersible pigment dispersion can be with 10 weight % to 20 weight %, such as 12 weights Amount % to 18 weight % amount are included.During dispersible pigment dispersion in comprising the scope, pigmentation, aobvious can be improved Shadow performance and contrast ratio.
Adhesive resin
Adhesive resin can include acryloyl base class (acryl-based) adhesive resin.
Acryl based binder resin is the first alkene system unsaturated monomer and can be with the diene series insatiable hunger of its combined polymerization And it is the resin for including at least one acryloyl base class repeat unit with the copolymer of monomer.
First alkene system unsaturated monomer is the alkene system unsaturated monomer for including at least one carboxyl.The example bag of the monomer Containing (methyl) acrylic acid, maleic acid, itaconic acid, fumaric acid or its combination.
Based on the total amount of acryl based binder resin, the first alkene system unsaturated monomer can be with 5 weight % to 50 weights % is measured, such as 10 weight % to 40 weight % amount are included.
Diene series unsaturated monomer can be aromatic ethenyl compound, such as styrene, α-methylstyrene, ethene Base toluene, vinyl benzene dimethyl cellosolve etc.；Unsaturated carboxylic ester compound, such as (methyl) methyl acrylate, (methyl) acrylic acid Ethyl ester, (methyl) butyl acrylate, (methyl) acrylic acid 2- hydroxy methacrylates, (methyl) acrylic acid 2- hydroxybutyls, (methyl) third Olefin(e) acid benzene methyl, (methyl) cyclohexyl acrylate, (methyl) phenyl acrylate etc.；Unsaturated carboxylic acid aminoalkyl ester compounds, Such as (methyl) acrylic acid 2- amino ethyl esters, (methyl) acrylic acid 2- dimethylaminoethyls；Generating vinyl carboxylate ester compounds, such as acetic acid Vinyl acetate, vinyl benzoate etc.；Unsaturated carboxylic acid glycidyl ester compounds, such as (methyl) glycidyl acrylate Deng；Vinyl cyanide compound, such as (methyl) acrylonitrile；Unsaturated acyl amines, such as (methyl) acrylamide；Etc., And can be individually or with two kinds or more than two kinds form of mixtures use.
The particular instance of acryl based binder resin can be polyphenyl methylmethacylate copolymer, propylene Acid/benzyl methacrylate copolymer, methacrylic acid/benzyl methacrylate copolymer, methacrylic acid/methyl-prop Olefin(e) acid benzene methyl/styrol copolymer, methacrylic acid/benzyl methacrylate/HEMA copolymer, Methacrylic acid/benzyl methacrylate/styrene/methacrylic acid 2- hydroxyl ethyl ester copolymers etc., but not limited to this.These It can be used alone or the form of mixtures with two kinds or more than two kinds uses.
The weight average molecular weight of adhesive resin can be 3,000 gram/mol to 150,000 grams/mol, such as 5, 000 gram/mol to 50,000 gram/mol, such as 20,000 gram/mol to 30,000 gram/mol.When adhesive resin has institute During weight average molecular weight in the range of stating, photosensitive resin composition has good physics during colored filter is manufactured With chemical characteristic, appropriate viscosity and close contact property with substrate.
Based on the total amount of photosensitive resin composition, adhesive resin can be with 1 weight % to 30 weight %, such as 1 weight Amount % to 20 weight % amount are included.During adhesive resin in comprising above range, due in manufacture colorized optical filtering Improved crosslinking during piece, developability can be improved and excellent surface smoothness can be improved.
Photopolymerizable compound
Photopolymerizable compound can include the simple function of at least one alkene system unsaturated double-bond (methyl) acrylic acid Or multifunctional ester.
Alkene system unsaturated double-bond is attributed to, photopolymerizable compound can cause in patterning process, during exposure The enough pattern of polymerization and formation with splendid heat resistance, light resistance and chemical resistance.
The particular instance of photopolymerizable compound can be two (methyl) acrylic acid glycol esters, two (methyl) acrylic acid two Glycol ester, two (methyl) acrylic acid triglycol esters, two (methyl) propylene acid propylene glycol esters, two (methyl) acrylic acid new penta 2 Alcohol ester, two (methyl) acrylic acid BDO esters, two (methyl) acrylic acid 1,6- hexylene glycols ester, bisphenol-A two (methyl) propylene Acid esters, two (methyl) acrylate, pentaerythritols, three (methyl) acrylate, pentaerythritols, four (methyl) acrylic acid pentaerythrites Ester, six (methyl) acrylate, pentaerythritols, two (methyl) acrylic acid dipentaerythritol esters, the season penta 4 of three (methyl) acrylic acid two Alcohol ester, five (methyl) acrylic acid dipentaerythritol esters, six (methyl) acrylic acid dipentaerythritol esters, bisphenol A epoxide resin (first Base) acrylate, ethylene glycol single methyl ether (methyl) acrylate, trimethylolpropane tris (methyl) acrylate, tricresyl phosphate (methyl) acryloyloxyethyl ester, novolac epoxy resin (methyl) acrylate etc..
The commercial examples of photopolymerizable compound can be as follows.Simple function (methyl) acrylate can include Ah's Knicks (Aronix)(East Asia synthetic chemical industry Co., Ltd. (Toagosei Chemistry Industry Co., Ltd.s))；Block sub- Randt (KAYARAD)(Nippon Kayaku K. K (Nippon Kayaku Co., Ltd.s)：(Osaka Organic Chemical Industry Co., Ltd. (Osaka Organic Chemical Ind., Ltd.)) etc..The example of difunctionality (methyl) acrylate can include Ah's Knicks(East Asia synthetic chemical industry Co., Ltd), the sub- rad of card(Nippon Kayaku K. K), V-335(Osaka has Chemical machine Industrial Co., Ltd) etc..The example of trifunctional (methyl) acrylate can include Ah's Knicks(East Asia synthetic chemical industry strain Formula commercial firm)；Block sub- rad(Japanese chemical drug strain Formula commercial firm)；(Osaka is by disproportionation medicine Industrial Co., Ltd (Osaka Yuki Kayaku Kogyo Co.Ltd.)) etc..These can be used alone or the mixture with two kinds or more than two kinds Form uses.
The photopolymerizable compound can be handled through acid anhydrides to improve developability.
Based on the total amount of photosensitive resin composition, photopolymerizable compound can be with 1 weight % to 15 weight %, such as 5 Weight % to 10 weight % amount are included.When the photopolymerizable compound in the scope, photopolymerizable Fully solidify during exposure of the compound in patterning process and there is fabulous reliability, and alkaline-based developer can be improved Developability.
Photopolymerization initiator
Photopolymerization initiator can be the photopolymerization initiator commonly used in photosensitive resin composition, such as acetophenones Compound, Benzophenone class compound, thioxanthene ketone class compound, styrax class compound, oxime compound etc..
The example of acetophenone compounds can be 2,2 '-diethoxy acetophenone, 2,2 '-dibutoxy acetophenone, 2- Hydroxy-2-methyl propiophenone, to tert-butyl group trichloroacetophenone, to tert-butyl group dichloroacetophenone, 4- chloro-acetophenones, 2,2 '-two is chloro- 4- metaphenoxy acetophenones, 2- methyl isophthalic acids-(4- (methyl mercapto) phenyl) -2- morpholinyl propyl- 1- ketone, 2- benzyl -2- dimethylaminos - 1- (4- morpholino phenyls)-butyl- 1- ketone etc..
The example of Benzophenone class compound can be benzophenone, benzoilbenzoate, benzoyl methyl benzoate, 4- phenyl benzophenones, dihydroxy benaophenonel, acrylated benzophenone, 4,4 '-bis- (dimethylamino) benzophenone, 4, 4 '-bis- (diethylamino) benzophenone, 4,4 '-dimethylamino benzopheone, 4,4 '-dichloro benzophenone, 3,3 '-diformazan Base -2- methoxy benzophenones etc..
The example of thioxanthene ketone class compound can be thioxanthones, 2- methyl thioxanthones, isopropyl thioxanthone, 2,4- diethyl Thioxanthones, 2,4- diisopropylthioxanthones, CTX etc..
The example of styrax class compound can be styrax, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, Benzoin isobutyl ether, benzyl dimethyl ketal etc..
The example of compound in triazine class can be 2,4,6- trichloto-s-triazines, double (the trichloromethyl)-s- of 2- phenyl -4,6- Double (the trichloromethyl)-s- triazines of triazine, 2- (3 ', 4 '-dimethoxy-styryl) -4,6-, 2- (4 '-methoxyl group naphthyl) -4, Double (the trichloromethyl)-s- triazines of 6-, double (the trichloromethyl)-s- triazines of 2- (p-methoxyphenyl) -4,6-, 2- (p-methylphenyl) -4, Double (the trichloromethyl)-s- triazines of 6-, double (the trichloromethyl)-s- triazines of 2- biphenyl -4,6-, double (trichloromethyl) -6- styryls - Double (the trichloromethyl)-s- triazines of s- triazines, 2- (naphthols 1- yls) -4,6-, the double (trichlorines of 2- (4- methoxynaphthol 1- yls) -4,6- Methyl)-s- triazines, double (the trichloromethyl) -6- sunflower base-s- triazines of 2-4-, double (trichloromethyl) -6- (the 4- methoxyl groups of 2-4- Styryl)-s- triazines etc..
The example of oxime compound can be O- acyls oxime compound, 2- (O- benzoyl oximes) -1- [4- (thiophenyl) benzene Base] -1,2- acetyl caproyls, 1- (O- acetyl oxime) -1- [9- ethyls -6- (2- methyl benzoyls) -9H- carbazole -3- bases] ethyl ketone, O- Carbethoxyl group-α-oxygen amino -1- phenyl propyl- 1- ketone etc..The particular instance of O- acyl oxime compounds can be 1,2- acetyl caproyls, 2- Dimethylamino -2- (4- methylbenzyls) -1- (4- morpholines -4- bases-phenyl)-butyl- 1- ketone, 1- (4- Phenylsulfanylphenyls)-butyl- 1, 2- diketone 2- oxime-O- benzoic ethers, 1- (4- Phenylsulfanylphenyls)-octane -1,2- diketone 2- oxime-O- benzoic ethers, 1- (4- benzene sulphur Base phenyl)-octyl- 1- ketoxime-O- acetic acid esters, 1- (4- Phenylsulfanylphenyls)-butyl- 1- ketoxime-O- acetic acid esters etc..
In addition to the compound, photopolymerization initiator can further include carbazole compound, cyclohexadione compounds, boric acid sulfonium Class compound, weight nitrogen compound, glyoxaline compound, bisglyoxaline class compound, compound of fluorene class etc..
The photopolymerization initiator can be with that can cause chemical reaction by absorbing light and become to excite and then transmit The sensitising agent of its energy is used together.
The example of the sensitising agent can be tetraethylene glycol pair -3-thiopropionate, -3- mercaptopropionic acids of pentaerythrite four Ester, four -3-thiopropionate of dipentaerythritol with and the like.
Based on the total amount of photosensitive resin composition, photopolymerization initiator can with 0.01 weight % to 10 weight %, such as 0.1 weight % to 5 weight % amount are included.During photopolymerization initiator in comprising the scope, due in pattern shape Fully solidify during exposure during, it can be ensured that splendid reliability, pattern there can be splendid resolution ratio and closely connect Characteristic and splendid heat resistance, light resistance and chemical resistance are touched, and due to non-reaction initiator, can prevent that transmissivity is bad Change.
Solvent
Solvent is gathered with the compound according to one embodiment, pigment, adhesive resin, photopolymerizable compound and light Close the material that initiator has compatibility but do not reacted.
The example of solvent can include alcohol, such as methanol, ethanol；Ether, such as dichloroether, n-butyl ether, isoamyl ether, methylbenzene Ether, tetrahydrofuran etc.；Glycol ethers, such as glycol monoethyl ether, ethylene glycol monoethyl ether；Ethylene glycol ethyl ethers acid ether, such as methyl second two Alcohol acetic acid ether, ethohexadiol acetic acid ether, diethyl ethylene glycol ethyl ethers acid ether etc.；Carbitol (carbitol), such as methyl Ethylcarbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol Ethyl methyl ether, diethylene glycol diethyl ether etc.；Propylene glycol alkyl ether acetic acid ester, such as propylene glycol methyl ether acetate, propylene glycol propyl ether acetic acid Ester etc.；Aromatic hydrocarbon, such as toluene, dimethylbenzene；Ketone, such as methyl ethyl ketone, cyclohexanone, 4- hydroxy-4-methyl-2-pentanones, first The positive acetone of base, methyl n-butyl ketone, Methylpentanone, 2-HEPTANONE etc.；Representative examples of saturated aliphatic monocarboxylic acid Arrcostab, such as ethyl acetate, second Sour N-butyl, isobutyl acetate etc.；Lactate, such as methyl lactate, ethyl lactate；Ethoxyacetic acid Arrcostab, such as ethoxyacetic acid Methyl esters, ethoxyacetic acid ethyl ester, ethoxyacetic acid butyl ester etc.；Alkoxy acetic acid Arrcostab, such as methoxy menthyl acetate, methoxyacetic acid Ethyl ester, methoxyacetic acid butyl ester, ethoxy acetate, ethoxy ethyl acetate etc.；3- epoxide alkyl propionates, such as 3- epoxides Methyl propionate, 3- epoxide ethyl propionates etc.；3- alkoxypropan acid alkyl esters, such as 3- methoxy methyl propionates, 3- methoxypropionic acids Ethyl ester, 3- ethoxyl ethyl propionates, 3- ethoxypropanoates etc.；2- epoxide alkyl propionates, such as 2- epoxides methyl propionate, 2- Epoxide ethyl propionate, 2- epoxide propyl propionates etc.；2- alkoxypropan acid alkyl esters, such as 2- methoxy methyl propionates, 2- methoxyl groups Ethyl propionate, 2- ethoxyl ethyl propionates, 2- ethoxypropanoates etc.；2- epoxides -2 Methylpropionic acid ester, such as 2- epoxides -2- Methylpropionic acid methyl esters, 2- epoxides -2 Methylpropionic acid ethyl ester etc.；2- alkoxies -2 Methylpropionic acid of single epoxide monocarboxylic acid Arrcostab Arrcostab, such as 2- methoxyl group -2 Methylpropionic acid methyl esters, 2- ethyoxyls -2 Methylpropionic acid ethyl ester；Ester, such as propionic acid 2- hydroxyl second Ester, propionic acid 2- hydroxy-2-methyls ethyl ester, acetic acid hydroxy methacrylate, butyric acid 2- hydroxy-3-methyl methyl esters etc.；Keto ester, such as pyruvic acid Ethyl ester etc..In addition it is also possible to using high boiling solvent, such as N-METHYLFORMAMIDE, DMF, N- methyl formyl benzene Amine, N- methylacetamides, DMA, 1-METHYLPYRROLIDONE, dimethyl sulfoxide, benzyl ether, two hexyl ethers, second Acyl acetone, isophorone (isophorone), caproic acid, octanoic acid, 1- octanols, 1 nonyl alcohol, phenmethylol, phenylmethyl acetate, benzoic acid Ethyl ester, diethy-aceto oxalate, diethyl maleate, gamma-butyrolacton, ethylene carbonate, propylene carbonate, ethylene glycol ethyl ether second Acid phenenyl ester etc..
In view of compatibility and reactivity, glycol ethers, such as ethylene glycol monoethyl ether can be preferably used；Ethylene glycol alkyl Ether acetic acid ester, such as ethohexadiol acetic acid ether；Ester, such as propionic acid 2- hydroxy methacrylates；Carbitol, such as diethylene glycol monomethyl ether Deng；Propylene glycol alkyl ether acetic acid ester, such as propylene glycol methyl ether acetate, propylene glycol propyl ether acetic acid esters；And ketone, such as hexamethylene Ketone.
Solvent is used with surplus, such as based on the total amount of photosensitive resin composition 30 weight % to 80 weight %.Work as bag During containing solvent in the scope, photosensitive resin composition can have proper viscosity, so as to improve the painting of colored filter Cloth feature.
Other additives
Other additives, such as malonic acid can be further included according to the photosensitive resin composition of one embodiment；3- amino -1, 2- propane diols；Silanes coupling agent, include vinyl or (methyl) acryloxy；Leveling agent；Surfactant；And freely Base polymerization initiators so as to adjust leveling, or prevent from being attributed to undeveloped pattern to prevent the spot or spot during coating Residue.
Required Characteristics Control additive can be depended on.
Coupling agent can be silanes coupling agent, and the example of silanes coupling agent can be trimethoxy silane Ji Benjia Acid, γ-methylacryloyl propoxyl group trimethoxy silane, vinyltriacetoxy silane, vinyltrimethoxy silane, γ-isocyanates propyl-triethoxysilicane, γ-glycidoxypropyltrimewasxysilane, β-(3,4- epoxycyclohexyethylSiOis Base) ethyl trimethoxy silane etc..These can be used alone or the form of mixtures with two kinds or more than two kinds uses.
Based on the total amount of photosensitive resin composition, silanes coupling agent can be with the amount bag of 0.01 parts by weight to 10 parts by weight Containing inside.
In addition, the photosensitive resin composition for colored filter can further include surfactant, such as fluorine class surface Activating agent.
The example of fluorine class surfactant can include Dainippon Ink. ＆ Chemicals Inc (DIC Co., Ltd.s) F-482, F-484, F-478 of manufacture etc., but not limited to this.
Based on the total amount of photosensitive resin composition, surfactant can be with 0.001 weight % to 5 weight %, preferably 0.01 weight % to 2 weight % amount are included.When the amount exceeds the scope, it is possible to create the external grain after development Son.
Epoxide can be further included according to the photosensitive resin composition of one embodiment to improve the adhesion to substrate Property.
The example of epoxide can include phenol novolac epoxy compound, tetramethyl biphenyl epoxide, bisphenol-A ring Oxygen compound, cycloaliphatic expoxy compounds or its combination.
Based on 100 parts by weight of photosensitive resin composition, epoxide can be with 0.01 parts by weight to 20 parts by weight, example Amount such as 0.1 parts by weight to 10 parts by weight is included.When the amount is in the scope, adhesiveness can be strengthened and deposited Storage.
In addition, unless additive makes the deterioration in characteristics of photosensitive resin composition, otherwise photosensitive resin composition can wrap Other additives containing scheduled volume, such as antioxidant, stabilizer.
According to another embodiment, there is provided the colored filter that a kind of use manufactures according to the photosensitive resin composition of embodiment Mating plate.
The method for manufacturing colored filter is as follows.
On a glass substrate in a suitable approach, such as spin coating, roller coating, spraying photosensitive resin coating constituent are to form 0.5 micron to 10 microns thick photosensitive resin composition layer.
Then, there is the substrate of photosensitive resin composition layer by light radiation to form pattern needed for colored filter. Radiation can by using UV, electron beam or X ray as light source progress, and UV can for example at 190 nanometers to 450 nanometers, And radiated in especially 200 nanometers to 400 nanometers of region.Radiation can enter by further using photoresist mask OK.After radiative process is carried out in this way, the photosensitive resin composition layer for being exposed to light source is handled with developer solution.At this Wen Zhong, non-exposed area dissolving in photosensitive resin composition layer and forms the pattern of colored filter.This process can repeat With the number of required number of color as many, the colored filter with required pattern is obtained.In addition, it ought pass through in the above-mentioned methods By the picture pattern that development obtains by reheating or when radiating photochemical actinic radiation-curable thereto, crack resistance, resistance to molten can be improved Agent etc..
Hereinafter, the present invention is described in more detail in reference example, however, but these examples not with any implication explain be limited The scope of the present invention processed.
(synthesis of compound)
Synthesize example 1：Synthesize 4- (biphenyl -2- bases epoxide) -3,5,6- tri- chloro- phthalonitriles
By 5 gram 3,4,5,6- tetrachloro phthalonitriles, 3.21 grams of 2- phenylphenols, 3.9 grams of K2CO3And 25 milliliters of acetone It is placed in 100 milliliters of flasks, and is followed by stirring for, while is heated at 70 DEG C.When the reactions are completed, gains are filtered and with third Ketone washs, and distills liquid therefrom to obtain solid.Herein, obtained solid dissolving is made in a small amount of dichloromethane In, and then washed several times with hexane, filter and be dried in vacuo to obtain 4- (biphenyl -2- bases epoxide) -3,5,6- tri- chloro- neighbours Benzene dicarbonitrile.
Synthesize example 2：Synthesize 3,4,6- tri- chloro- 5- (2,6- dichloro-phenoxy)-phthalonitrile
By 5 gram 3,4,5,6- tetrachloro phthalonitriles, 3.06 grams of 2,6- chlorophenesic acids, 3.9 grams of K2CO3And 25 milliliter third Ketone is placed in 100 milliliters of flasks, and is followed by stirring for, while is heated at 70 DEG C.When the reactions are completed, gains and use are filtered Acetone washs, and distills liquid therefrom to obtain solid.Herein, obtained solid dissolving is made in a small amount of dichloromethane In alkane, and then washed several times with hexane, filter and be dried in vacuo to obtain 3,4,6- tri- chloro- 5- (2,6- bis- chloro- benzene oxygen Base)-phthalonitrile.
Synthesize example 3：Synthesize 3,4,6- tri- chloro- 5- (2,6- dibromo-phenoxy)-phthalonitrile
By 5 gram 3,4,5,6- tetrachloro phthalonitriles, 4.75 grams of 2,6- dibromophenols, 3.9 grams of K2CO3And 25 milliliters of N, Dinethylformamide is placed in 100 milliliters of flasks, and is stirred, while is heated at 70 DEG C.When the reactions are completed, EA (second Acetoacetic ester) it is used to extract.After extraction, gains are concentrated to obtain solid.Make obtained solid dissolving in a small amount of dichloro In methane, washed several times with hexane, filter and be dried in vacuo to obtain 3,4,6- tri- chloro- 5- (2,6- dibromo-phenoxy)-neighbour Benzene dicarbonitrile.
Synthesize example 4：Synthesize 3,4,6- tri- chloro- 5- (2,6- dilquoro-phenogy)-phthalonitrile
By 5 gram 3,4,5,6- tetrachloro phthalonitriles, 2.45 grams of 2,6- difluorophenols, 3.9 grams of K2CO3And 25 milliliters of N, Dinethylformamide is placed in 100 milliliters of flasks, and is followed by stirring for, while is heated at 70 DEG C.When the reactions are completed, EA (ethyl acetate) is used to extract.After extraction, gains are concentrated to obtain solid.Herein, make obtained solid molten Solution is then washed several times in a small amount of dichloromethane with hexane, is filtered and is dried in vacuo to obtain 3,4,6- tri- chloro- 5- (2,6- dilquoro-phenogy)-phthalonitrile.
Synthesize example 5：Synthesize 3,4,6- tri- chloro- 5- (the chloro- phenoxy groups of 2-)-phthalonitrile
By 5 gram 3,4,5,6- tetrachloro phthalonitriles, 2.41 grams of 2- chlorophenols, 3.9 grams of K2CO3And 25 milliliters of acetone are put Put in 100 milliliters of flasks, and be followed by stirring for, while heated at 70 DEG C.When the reactions are completed, gains are filtered and use acetone Washing, distills liquid therefrom to obtain solid.Herein, obtained solid dissolving is made in a small amount of dichloromethane In, washed several times with hexane, filter and be then dried in vacuo to obtain 3,4,6- tri- chloro- 5- (the chloro- phenoxy groups of 2-)-adjacent benzene two Formonitrile HCN.
Synthesize example 6：Synthesize 3,4,6- tri- chloro- 5- (the bromo- phenoxy groups of 2-)-phthalonitrile
By 5 gram 3,4,5,6- tetrachloro phthalonitriles, 3.25 grams of 2- bromophenols, 3.9 grams of K2CO3And 25 milliliters of N, N- bis- NMF is placed in 100 milliliters of flasks, and is followed by stirring for, while is heated at 70 DEG C.When the reactions are completed, EA (second Acetoacetic ester) it is used to extract.After extraction, gains are concentrated to obtain solid.Herein, make obtained solid dissolving in In a small amount of dichloromethane, washed several times with hexane, filter and be dried in vacuo to obtain 3,4,6- tri- chloro- 5- (the bromo- benzene oxygen of 2- Base)-phthalonitrile.
Synthesize example 7：Synthesize 3,4,6- tri- chloro- 5- (the fluoro- phenoxy groups of 2-)-phthalonitrile
By 5 gram 3,4,5,6- tetrachloro phthalonitriles, 2.10 grams of 2- fluorophenols, 3.9 grams of K2CO3And 25 milliliters of N, N- bis- NMF is placed in 100 milliliters of flasks, and is followed by stirring for, while is heated at 70 DEG C.When the reactions are completed, EA (second Acetoacetic ester) it is used to extract.After extraction, gains are concentrated to obtain solid.Make obtained solid dissolving in a small amount of dichloro In methane, washed several times with hexane, filter and be dried in vacuo to obtain 3,4,6- tri- chloro- 5- (the fluoro- phenoxy groups of 2-)-adjacent benzene two Formonitrile HCN.
Synthesize example 8：Synthesize 3,4,6- tri- chloro- 5- (2,5- dichloro-phenoxy)-phthalonitrile
By 5 gram 3,4,5,6- tetrachloro phthalonitriles, 3.06 grams of 2,5- chlorophenesic acids, 3.9 grams of K2CO3And 25 milliliter third Ketone is placed in 100 milliliters of flasks, and is followed by stirring for, while is heated at 70 DEG C.When the reactions are completed, gains and use are filtered Acetone washs, and distills liquid therefrom to obtain solid.Herein, obtained solid dissolving is made in a small amount of dichloromethane In alkane, washed several times with hexane, filter and be dried in vacuo to obtain 3,4,6- tri- chloro- 5- (2,5- dichloro-phenoxy)-adjacent benzene Dimethoxy nitrile.
Synthesize example 9：Synthesize the compound represented by chemical formula 5
By 4- (biphenyl -2- bases epoxide) -3,5,6- tri- chloro- phthalonitriles of 1.5 grams of synthesis examples 1,0.49 gram of synthesis The 3 of example 2,4,6- tri- chloro- 5- (2,6- dichloro-phenoxy)-phthalonitriles, 1.52 grams of -7- of 1,8- diazabicyclos 11 Alkene and 14 grams of 1- pentenols are placed in 100 milliliters of flasks, and are then heated at 90 DEG C, after solid dissolving, Xiang Qi 0.23 gram of zinc acetate of middle addition, and mixture is stirred, while heated at 140 DEG C.When the reactions are completed, methanol is used to precipitate, And filtering sediment therefrom and vacuum drying.Dry solid passes through column chromatography eluting.Then, dichloromethane is fitted Locality is added in purified solid so that it dissolves, and adds methanol thereto to crystallize.Filtering for crystallizing solid and true Sky is dried to obtain the compound represented by chemical formula 5.
[chemical formula 5]
Maldi-tof MS：1656.79m/z
Synthesize example 10：Synthesize the compound represented by chemical formula 6
By 1.6 grams of 4- (biphenyl -2- bases epoxide) -3,5,6- tri- chloro- phthalonitriles, 1.5 grams of roots according to synthesis example 1 According to 3,4,6- tri- chloro- 5- (2,6- dichloro-phenoxy)-phthalonitriles, 1.74 grams of 1, the 8- diazabicyclos ten of synthesis example 2 One -7- alkene and 14 grams of 1- pentenols are placed in 100 milliliters of flasks, and are heated at 90 DEG C, after solid dissolving, Xiang Qi 0.34 gram of zinc acetate of middle addition, and mixture is stirred, while heated at 140 DEG C.When the reactions are completed, methanol is used to precipitate, And filtering sediment therefrom and vacuum drying.Dry solid passes through column chromatography eluting.Then, dichloromethane is fitted Locality is added in purified solid and makes its dissolving, and adds methanol thereto to crystallize.Filtering for crystallizing solid and true Sky is dried to obtain the compound represented by chemical formula 6.
[chemical formula 6]
Maldi-tof MS：1649.57m/z
Synthesize example 11：Synthesize the compound represented by chemical formula 7
By 4- (biphenyl -2- bases epoxide) -3,5,6- tri- chloro- phthalonitriles of 1 gram of synthesis example 1,2.9 grams of synthesis examples The 3 of 2,4,6- tri- chloro- 5- (2,6- dichloro-phenoxy)-phthalonitriles, 3 grams of -7- alkene of 1,8- diazabicyclos 11 and 27 Gram 1- pentenols are placed in 100 milliliters of flasks, and are heated at 90 DEG C, after solid dissolving, add 0.45 gram thereto Zinc acetate, and mixture is stirred, while heated at 140 DEG C.When the reactions are completed, methanol is used to precipitate, and filtering is obtained by it The sediment arrived and vacuum drying.Dry solid passes through column chromatography eluting.Then, dichloromethane is suitably added to through So that it dissolves in the solid of purifying, and methanol is added thereto to crystallize.Filtering for crystallizing solid and vacuum drying is to obtain The compound represented by chemical formula 7.
[chemical formula 7]
Maldi-tot MS：1642.36m/z
Synthesize example 12：Synthesize the compound represented by chemical formula 8
By 1.5 grams synthesis example 23,4,6- tri- chloro- 5- (2,6- dichloro-phenoxy)-phthalonitriles, 0.87 gram 1, - 7- the alkene of 8- diazabicyclos 11 and 7 grams of 1- pentenols are placed in 100 milliliters of flasks, and are then heated at 90 DEG C, After solid dissolving, 0.17 gram of zinc acetate is added thereto, and stirs mixture, while is heated at 140 DEG C.When reaction is completed When, methanol is used to precipitate, and filters sediment therefrom and vacuum drying.Dry solid passes through column chromatography eluting. Then, dichloromethane is suitably added in purified solid so that it dissolves, and adds methanol thereto to crystallize. Filtering for crystallizing solid and vacuum drying is to obtain the compound represented by chemical formula 8.
[chemical formula 8]
Maldi-tof MS：1635.14m/z
Synthesize example 13：Synthesize the compound represented by chemical formula 9
By 1.5 grams synthesis example 33,4,6- tri- chloro- 5- (2,6- dibromo-phenoxy)-phthalonitriles, 0.87 gram 1, - 7- the alkene of 8- diazabicyclos 11 and 7 grams of 1- pentenols are placed in 100 milliliters of flasks, and are then heated at 90 DEG C, After solid dissolving, 0.17 gram of zinc acetate is added thereto, and stirs mixture, while is heated at 140 DEG C.When reaction is completed When, methanol is used to precipitate, and filters sediment therefrom and vacuum drying.Dry solid passes through column chromatography eluting. Then, dichloromethane is suitably added in purified solid, and methanol is used to crystallize.Filtering for crystallizing solid and vacuum is done The dry compound represented with acquisition by chemical formula 9.
[chemical formula 9]
Maldi-tof MS：1990.78m/z
Synthesize example 14：Synthesize the compound represented by chemical formula 10
By 1.5 grams synthesis example 43,4,6- tri- chloro- 5- (2,6 dilquoro-phenogy)-phthalonitriles, 0.87 gram 1,8- - 7- the alkene of diazabicyclo 11 and 7 grams of 1- pentenols are placed in 100 milliliters of flasks, and are heated at 90 DEG C, molten in solid After solution, 0.17 gram of zinc acetate is added thereto, and stirs mixture, while is heated at 140 DEG C.When the reactions are completed, first Alcohol is used to precipitate, and filters sediment therefrom and vacuum drying.Dry solid passes through column chromatography eluting.Then, Dichloromethane is suitably added in purified solid, and adds methanol thereto to crystallize.Filtering for crystallizing solid and It is dried in vacuo to obtain the compound represented by chemical formula 10.
[chemical formula 10]
Maldi-tof MS：1503.53m/z
Synthesize example 15：Synthesize the compound represented by chemical formula 11
By 3,4,6- tri- chloro- 5- (the chloro- phenoxy groups of 2-)-phthalonitriles, 0.87 gram of 1, the 8- bis- of 1.5 grams of synthesis examples 5 - 7- the alkene of azabicyclo 11 and 7 grams of 1- pentenols are placed in 100 milliliters of flasks, and are heated at 90 DEG C, in solid dissolving Afterwards, 0.17 gram of zinc acetate is added thereto, and stirs mixture, while is heated at 140 DEG C.When the reactions are completed, methanol For precipitating, and filtering precipitate and vacuum drying.Dry solid passes through column chromatography eluting.Then, dichloromethane is fitted Locality is added in purified solid so that it dissolves, and adds methanol thereto to crystallize.Filtering for crystallizing solid and true Sky is dried to obtain the compound represented by chemical formula 11.
[chemical formula 11]
Maldi-tof MS：1497.38m/z
Synthesize example 16：Synthesize the compound represented by chemical formula 12
By 3,4,6- tri- chloro- 5- (the bromo- phenoxy groups of 2-)-phthalonitriles, 0.87 gram of 1, the 8- bis- of 1.5 grams of synthesis examples 6 - 7- the alkene of azabicyclo 11 and 7 grams of 1- pentenols are placed in 100 milliliters of flasks, and are heated at 90 DEG C, in solid dissolving Afterwards, 0.17 gram of zinc acetate is added thereto, and stirs mixture, while is heated at 140 DEG C.When the reactions are completed, methanol For precipitating, and filter sediment therefrom and vacuum drying.Dry solid passes through column chromatography eluting.Then, will Dichloromethane is suitably added in purified solid so that it dissolves, and adds methanol thereto to crystallize.Filtering knot Brilliant solid and vacuum drying is to obtain the compound represented by chemical formula 12.
[chemical formula 12]
Maldi-tof MS：1675.19m/z
Synthesize example 17：Synthesize the compound represented by chemical formula 13
By 3,4,6- tri- chloro- 5- (the fluoro- phenoxy groups of 2-)-phthalonitriles, 0.87 gram of 1, the 8- bis- of 1.5 grams of synthesis examples 7 - 7- the alkene of azabicyclo 11 and 7 grams of 1- pentenols are placed in 100 milliliters of flasks, and are heated at 90 DEG C, in solid dissolving Afterwards, 0.17 gram of zinc acetate is added thereto, and stirs mixture, while is heated at 140 DEG C.When the reactions are completed, methanol For precipitating, and filter sediment therefrom and vacuum drying.Dry solid passes through column chromatography eluting.Then, will Dichloromethane is suitably added in purified solid so that it dissolves, and adds methanol thereto to crystallize.Filtering knot Brilliant solid and vacuum drying is to obtain the compound represented by chemical formula 13.
[chemical formula 13]
Maldi-tof MS：1431.57m/z
Synthesize example 18：Synthesize the compound represented by chemical formula 14
4- (biphenyl -2- bases epoxide) -3,5,6- tri- chloro- phthalonitriles of 1.6 grams of synthesis examples 1,1.5 grams of synthesis are real The 3 of example 8,4,6- tri- chloro- 5- (2,5- dichloro-phenoxy)-phthalonitriles, 1.74 grams of -7- alkene of 1,8- diazabicyclos 11 And 14 grams of 1- pentenols are placed in 100 milliliters of flasks, and heat at 90 DEG C, after solid dissolving, add thereto 0.34 gram of zinc acetate, and mixture is stirred, while heated at 140 DEG C.When the reactions are completed, methanol is used to precipitate, and filters Sediment therefrom and vacuum drying.Dry solid passes through column chromatography eluting.Then, dichloromethane is suitably added It is added in purified solid so that it dissolves, and adds methanol thereto to crystallize.Filtering for crystallizing solid and vacuum drying To obtain the compound represented by chemical formula 14.
[chemical formula 14]
Maldi-tof MS：1649.57m/z
Compare synthesis example 1：Synthesize the compound represented by chemical formula X
By -3,5,6- tri- chloro- phthalonitriles of 1 gram of 4- (2- sec-butyls-phenoxy group), 0.30 gram of 1,8- diazabicyclo ten One -7- alkene, 7 grams of 1- pentenols and 0.12 gram of zinc acetate are placed in 100 milliliters of flasks, and are stirred, while are added at 140 DEG C Heat.When the reactions are completed, gains are concentrated and by column chromatography eluting.Purified liquid is concentrated to obtain solid.Vacuum Drying crystalline solid is to obtain the compound represented by chemical formula X.
[chemical formula X]
Maldi-tof MS：1584.04m/z
(synthesis of photosensitive resin composition)
Example 1
By mixing following components to be formed shown in table 1 to prepare the photosensitive resin composition according to example 1.
Exactly, photopolymerization initiator is dissolved in solvent, solution is stirred at room temperature 2 hours, adds thereto Adhesive resin and photopolymerizable compound, and mixture is stirred at room temperature 2 hours.Then, the compound of example 9 will be synthesized (being represented by chemical formula 5) and pigment as colouring agent are added in reactant (under pigment dispersity), and at room temperature Stir mixture 1 hour.Then, product therefrom is filtered three times to go the removal of impurity, so as to prepare photoresist composition Thing.
[table 1]
(unit：Weight %)
Example 2
Except the compound for replacing synthesizing example 9 using the compound (being represented by chemical formula 6) of synthesis example 10 is (by chemistry Formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 1.
Example 3
Except the compound for replacing synthesizing example 9 using the compound (being represented by chemical formula 7) of synthesis example 11 is (by chemistry Formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 1.
Example 4
Except the compound for replacing synthesizing example 9 using the compound (being represented by chemical formula 8) of synthesis example 12 is (by chemistry Formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 1.
Example 5
Except the compound for replacing synthesizing example 9 using the compound (being represented by chemical formula 9) of synthesis example 13 is (by chemistry Formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 1.
Example 6
Except the compound for replacing synthesizing example 9 using the compound (being represented by chemical formula 10) of synthesis example 14 is (by changing Formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 1.
Example 7
Except the compound for replacing synthesizing example 9 using the compound (being represented by chemical formula 11) of synthesis example 15 is (by changing Formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 1.
Example 8
Except the compound for replacing synthesizing example 9 using the compound (being represented by chemical formula 12) of synthesis example 16 is (by changing Formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 1.
Example 9
Except the compound for replacing synthesizing example 9 using the compound (being represented by chemical formula 13) of synthesis example 17 is (by changing Formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 1.
Example 10
Except the compound for replacing synthesizing example 9 using the compound (being represented by chemical formula 14) of synthesis example 18 is (by changing Formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 1.
Example 11
Except replacing 5 weight % dyestuffs using 3.7 weight % dyestuffs, " 2.5 weight % pigment G58 dispersible pigment dispersions are used With 13.7 weight % pigment Y138 dispersible pigment dispersions " replacement " 15.0 weight % pigment Y138 dispersible pigment dispersions ", and use 30.1 Weight %PGMEA is replaced beyond 30.0 weight %PGMEA, is formed according to the identical method of example 1 to prepare photoresist Thing.
Example 12
Except the compound for replacing synthesizing example 9 using the compound (being represented by chemical formula 6) of synthesis example 10 is (by chemistry Formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 11.
Example 13
Except the compound for replacing synthesizing example 9 using the compound (being represented by chemical formula 7) of synthesis example 11 is (by chemistry Formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 11.
Example 14
Except the compound for replacing synthesizing example 9 using the compound (being represented by chemical formula 8) of synthesis example 12 is (by chemistry Formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 11.
Example 15
Except the compound for replacing synthesizing example 9 using the compound (being represented by chemical formula 9) of synthesis example 13 is (by chemistry Formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 11.
Example 16
Except the compound for replacing synthesizing example 9 using the compound (being represented by chemical formula 10) of synthesis example 14 is (by changing Formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 11.
Example 17
Except the compound for replacing synthesizing example 9 using the compound (being represented by chemical formula 11) of synthesis example 15 is (by changing Formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 11.
Example 18
Except the compound for replacing synthesizing example 9 using the compound (being represented by chemical formula 12) of synthesis example 16 is (by changing Formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 11.
Example 19
Except the compound for replacing synthesizing example 9 using the compound (being represented by chemical formula 13) of synthesis example 17 is (by changing Formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 11.
Example 20
Except the compound for replacing synthesizing example 9 using the compound (being represented by chemical formula 14) of synthesis example 18 is (by changing Formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 11.
Comparative example 1
Except using compare synthesis example 1 compound (being represented by chemical formula X) replace synthesize example 9 compound (by Chemical formula 5 represents) beyond, prepare photosensitive resin composition according to the identical method of example 1.
Comparative example 2
In addition to the consisting of in table 2 replaces forming and mixed in table 1, according to the identical side of example 1 Method prepares photosensitive resin composition.
[table 2]
(unit：Weight %)
Assess 1：Assess brightness and contrast ratio
It will be respectively coated according to the photosensitive resin composition of example 1 to 20 and comparative example 1 and 2 as 1 micron to 3 microns It is thick and then to be dried 2 minutes on 90 DEG C of hot plates in the glass substrate of 1 millimeters thick degreasing, obtain film.Film is by using main Wavelength is 365 nanometers of high-pressure sodium lamp exposure.Then, film dries 5 minutes to obtain sample in boiler is dried in 200 DEG C of forced convertions Product.By using spectrophotometer (MCPD3000, great Zhong Electronics Co., Ltd (Otsuka Electronics Co., Ltd.s)) Brightness (Y) and the contrast ratio of pixel layer are measured, and result is provided in table 3.
[table 3]
Referring to table 3, compared to the photosensitive resin composition of comparative example 1 and 2, the compound according to one embodiment is included As the photosensitive resin composition of the example 1 to 20 of dyestuff, the photosensitive resin composition of especially example 1 to 9 shows splendid Color characteristic.
Although the present invention is combined to be currently considered to practical example embodiment to describe, it should be appreciated that the present invention is unlimited In disclosed embodiment, but on the contrary, it is contemplated that cover included in the spirit and scopes of appended claims it is each Kind modification and equivalent.

Claims (17)

  1. A kind of 1. compound represented by chemical formula 1：
    [chemical formula 1]
    In chemical formula 1,
    R1To R16Be independently hydrogen atom, halogen atom, C1 to the C20 alkyl for being substituted or being unsubstituted, be substituted or without Substituted C3 to C20 alkoxies, C6 to the C20 aryl for being substituted or being unsubstituted or C6 to the C20 for being substituted or being unsubstituted Aryloxy group,
    Restrictive condition is R1To R16In it is at least one represented by chemical formula 2,
    [chemical formula 2]
    Wherein in chemical formula 2,
    R17And R18It is independently halogen atom,
    N1 and n2 is independently the integer in the range of 0 to 5, and 1≤n1+n2≤5.
  2. 2. compound according to claim 1, wherein chemical formula 2 are by selected in chemical formula 3-1 to chemical formula 3-4 one Represent：
    [chemical formula 3-1]
    [chemical formula 3-2]
    [chemical formula 3-3]
    [chemical formula 3-4]
    Wherein in chemical formula 3-1 to chemical formula 3-4,
    R17And R18It is independently halogen atom.
  3. 3. compound according to claim 1, wherein R1To R16In it is at least one represented by chemical formula 2, and R1Arrive R16In at least one represented by chemical formula 4：
    [chemical formula 4]
  4. 4. compound according to claim 3, wherein R1To R16In it is at least one represented by chemical formula 2,
    R5To R8In it is at least one represented by chemical formula 4,
    R9To R12In it is at least one represented by chemical formula 4, and
    R13To R16In at least one represented by chemical formula 4.
  5. 5. compound according to claim 3, wherein R1To R4In it is at least one represented by chemical formula 2,
    R5To R8In it is at least one represented by chemical formula 2,
    R9To R12In it is at least one represented by chemical formula 4, and
    R13To R16In at least one represented by chemical formula 4.
  6. 6. compound according to claim 3, wherein R1To R4In it is at least one represented by chemical formula 2,
    R5To R8In it is at least one represented by chemical formula 4,
    R9To R12In it is at least one represented by chemical formula 2, and
    R13To R16In at least one represented by chemical formula 4.
  7. 7. compound according to claim 3, wherein R1To R4In it is at least one represented by chemical formula 2,
    R5To R8In it is at least one represented by chemical formula 2,
    R9To R12In it is at least one represented by chemical formula 2, and
    R13To R16In at least one represented by chemical formula 4.
  8. 8. compound according to claim 1, wherein R1To R4In it is at least one represented by chemical formula 2,
    R5To R8In it is at least one represented by chemical formula 2,
    R9To R12In it is at least one represented by chemical formula 2, and
    R13To R16In at least one represented by chemical formula 2.
  9. 9. compound according to claim 1, wherein it is described by the compound that chemical formula 1 represents by chemical formula 5 to chemistry An expression in formula 14：
    [chemical formula 5]
    [chemical formula 6]
    [chemical formula 7]
    [chemical formula 8]
    [chemical formula 9]
    [chemical formula 10]
    [chemical formula 11]
    [chemical formula 12]
    [chemical formula 13]
    [chemical formula 14]
  10. 10. compound according to claim 1, wherein the compound is green colouring material.
  11. 11. compound according to claim 10, wherein the green colouring material is at 445 nanometers to 560 nanometer wavelength ranges In there is maximum transmission rate.
  12. 12. a kind of photosensitive resin composition, including according to any claim in claim 1 to claim 11 Compound.
  13. 13. photosensitive resin composition according to claim 12, wherein the photosensitive resin composition, which includes, presses institute The weight % of total amount meter 1 of photosensitive resin composition is stated to the 10 weight % compound.
  14. 14. photosensitive resin composition according to claim 12, wherein the photosensitive resin composition further include it is viscous Mixture resin, photopolymerizable compound, photopolymerization initiator and solvent.
  15. 15. photosensitive resin composition according to claim 12, wherein the photosensitive resin composition further includes face Material.
  16. 16. photosensitive resin composition according to claim 15, wherein the pigment includes yellow uitramarine, viridine green Or its combination.
  17. 17. a kind of colored filter, manufactured using photosensitive resin composition according to claim 12.
CN201710177372.5A 2016-06-16 2017-03-23 Novel compound, photosensitive resin composition containing same and color filter Active CN107522704B (en)

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CN108957951B (en) * 2017-05-17 2021-11-02 三星Sdi株式会社 Photosensitive resin composition, photosensitive resin layer using same, and color filter

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